Imidiazoles having reduced side effects
View Patent ↗Methods and compounds for the treatment of conditions including pain, particularly chronic pain, glaucoma or elevated intraocular pressure with reduced cardiovascular or sedative side effects. Also included are methods of making and using such compounds.
1. A compound selected from the group consisting of:
wherein R 1 is independently selected from the group consisting of H; halogen; C 1-4 alkyl; C 1-4 alkenyl; C 1-4 alkynyl; —COR 4 where R 4 is H, C 1-4 alkyl or C 1-4 alkoxy; C 3-6 cycloalkyl; aryl; cyano; nitro; trihalomethyl; oxo; or —(CH 2 ) n —X—(CH 2 ) m —(R 5 ) o — where X is O, S or N, n is 0-3, m is 0-3, o is 0-1, and R 5 is methyl or H 1-2 , each R 6 is independent selected from the group consisting of H; halogen; C 1-4 alkyl; C 1-4 alkenyl; C 1-4 alkynyl; —COR 4 where R 4 is H, C 1-4 alkyl or C 1-4 alkoxy; C 3-6 cycloalkyl; aryl; cyano; nitro; trihalomethyl and oxo wherein each p is independently 1 or 2 and Y is —(C(R 7 ) z ) 2 —, wherein R 7 is independently defined identically to R 1 and z is independently 1 or 2, said compound further having selective agonist activity at the α2B or α2B/α2C adrenergic receptor subtype(s) over the α2A adrenergic receptor subtype, and all pharmacologically acceptable salts, esters, stereoisomers and racemic mixtures thereof.
2. The compound of claim 1 wherein Y is CH 2 —CH 2 .
3. The compound of claim 1 wherein R 1 , R 6 and R 7 are independently H; halogen; C 1-4 alkyl; C 1-4 alkenyl; or C 1-4 alkynyl.
4. The compound of claim 1 wherein Y is CH 2 —CH 2 and R 1 , R 6 and R 7 are independently H; halogen; C 1-4 alkyl; C 1-4 alkenyl; or C 1-4 alkynyl.
5. The compound of claim 4 wherein R 1 is H and x is 2.
6. The compound of claim 4 wherein at least one R 6 is H.
7. The compound of claim 6 wherein at least two R 6 are H.
8. The compound of claim 7 wherein at least three R 6 are H.
9. The compound of claim 8 wherein at least six R 6 are H.
10. The compound of claim 8 wherein eight R 6 are H.
11. The compound of claim 3 wherein R 1 is H and x is 2.
12. The compound of claim 11 wherein at least one R 6 is H.
13. The compound of claim 12 wherein at least two R 6 are H.
14. The compound of claim 13 wherein at least three R 6 are H.
15. The compound of claim 14 wherein at least six R 6 are H.
16. The compound of claim 15 wherein eight R 6 are H.
17. The compound of claim 16 in which R 1 is H and x is 2.
18. The compound of claim 17 in which Y is —CH 2 —CH 2 —.